Drew Barrymore in Never Been Kissed (1999)

Drew Barrymore, David Arquette, Jessica Alba, Marley Shelton, Jordan Ladd, and Michael Vartan in Never Been Kissed (1999)

Drew Barrymore and Dougray Scott in Ever After: A Cinderella Story (1998)

Drew Barrymore and John Cusack in Say Anything (1989)

Drew Barrymore in Ever After: A Cinderella Story (1998)

Mike Stoklasa in Never Been Kissed (1999)

Jessica Alba, Marley Shelton, and Jordan Ladd in Never Been Kissed (1999)

Drew Barrymore, Jessica Alba, Marley Shelton, and Jordan Ladd in Never Been Kissed (1999)

Drew Barrymore and Michael Vartan in Never Been Kissed (1999)

Leelee Sobieski in Never Been Kissed (1999)

David Arquette, Jessica Alba, and Katie Lansdale in Never Been Kissed (1999)

Drew Barrymore and Leelee Sobieski in Never Been Kissed (1999)

Drew Barrymore, Giuseppe Andrews, and Leelee Sobieski in Never Been Kissed (1999)

David Arquette in Never Been Kissed (1999)

Drew Barrymore and David Arquette in Never Been Kissed (1999)

Jessica Alba, Marley Shelton, James Franco, Jeremy Jordan, Jordan Ladd, and Branden Williams in Never Been Kissed (1999)

Drew Barrymore, Garry Marshall, and Molly Shannon in Never Been Kissed (1999)

Drew Barrymore, David Arquette, Jessica Alba, Marley Shelton, Leelee Sobieski, Jordan Ladd, and Michael Vartan in Never Been Kissed (1999)

Drew Barrymore, David Arquette, Jessica Alba, and Marley Shelton in Never Been Kissed (1999)

Drew Barrymore, Jessica Alba, and Marley Shelton in Never Been Kissed (1999)